Water → 3-Hydroxy-4-methoxy-3-phenyl-butyraldehyde

HRID 1191728Notes

Reaction equation

HRID 1191728 reaction equation
[CH3:1][O:2][CH2:3][C:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([OH:10])[CH2:5][CH:6]([OH:9])CO.O>ClCCl>[OH:10][C:4]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([CH2:3][O:2][CH3:1])[CH2:5][CH:6]=[O:9]

Participants

4

Reactant 2

HCID 962Water2×HCID 596356585-Methoxy-4-phenyl-pentane-1,2,4-triol

Product 1

HCID 596356773-Hydroxy-4-methoxy-3-phenyl-butyraldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

NaIO4 (5.20 g) was added to a mixture of 5-methoxy-4-phenyl-pentane-1,2,4-triol (1.10 g), dichloromethane (10 mL), and water (5 mL) chilled in an ice bath. The mixture was stirred vigorously while warming to ambient temperature in the cooling bath and further stirred at this temperature overnight. Then, water (20 mL) and dichloromethane (50 mL) were added, the organic layer was separated, and the aqueous layer was extracted with dichloromethane (2×25 mL). The combined organic phases were washed with water and dried (MgSO4). After removal of the solvent, the title compound was yielded which was directly submitted to the next reaction step (glycol cleavage).

Workup

  1. temperaturechilled in an ice bath
  2. stirringfurther stirred at this temperature overnight
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane (2×25 mL)
  5. washThe combined organic phases were washed with water
  6. dry with materialdried (MgSO4)
  7. customAfter removal of the solvent

Sources & evidence

ORD record
ord-1a3613152379489db5faaf518e88b1e9
Source dataset
uspto-grants-2014_03
Patent number
US08680093B2

Reaction notes

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